2-METHYL-PENT-4-ENAL synthesis
- Product Name:2-METHYL-PENT-4-ENAL
- CAS Number:5187-71-3
- Molecular formula:C6H10O
- Molecular Weight:98.14
5673-98-3
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Yield: 100%
Reaction Conditions:
Stage #1:2-methylpent-4-en-1-ol with oxalyl dichloride;dimethyl sulfoxide in dichloromethane at -60; for 0.25 h;Inert atmosphere;
Stage #2: with triethylamine in dichloromethane at 20; for 0.333333 h;
Steps:
44.1
To a solution of oxalyl chloride (6.65 mL, 74.9 mmol) in DCM (30 mL) at -60°C was added a solution of DMSO anhydrous (10.62 mL, 150 mmol) in DCM (20 mL) under N2 and stirred for 2 min. A solution of 2-methylpent-4-en- l-ol (5.00 g, 49.9 mmol) in DCM (20 mL) was added, and the resulting mixture was stirred for 15 min at -60°C. EtsN (34.7 mL, 250 mmol) was then added and the reaction mixture was stirred at ambient temperature for 20 min. The mixture was quenched with DCM and H20. The organic layer was washed with brine, dried (MgS04), and filtered. The filtrate was concentrated to afford the title compound (4.90 g, 100 %) without further purification.
References:
AMGEN INC.;BROWN, Sean P.;LI, Yunxiao;LIZARZABURU, Mike Elias;LUCAS, Brian S.;PARAS, Nick A.;TAYGERLY, Joshua;VIMOLRATANA, Marc;WANG, Xianghong;YU, Ming;ZANCANELLA, Manuel;ZHU, Liusheng;GONZALEZ BUENROSTRO, Ana;LI, Zhihong WO2016/33486, 2016, A1 Location in patent:Page/Page column 178
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